Perfect Match
by EZ11
Summary: COMPLETE. It's Valentine's Day on the Upper East Side and this year, Constance Billard and St. Judes are running an online personality survey called Perfect Match. C/B Season 1 FULL SUMMARY INSIDE.
1. One

A/N: I'm back! I know its been forever but life has been crazy and school has been insanely busy. But I'm back now and starting my new fic! this one will be much lighter then my last one and is set in the past- well during season 1. Anyway this was inspired by similar events in the it girl series classic, and this series is amazing btw,- but if you know the storyline it is only inspired, not following it completely due to obviously different characters and such. Ok I'll stop now so here we go…

**SUMMARY: It's Valentine's Day on the Upper East Side and this year Constance Billard and St. Judes are running an online personality survey called Perfect Match-supposedly to match each student with their perfect soul mate. Blair is convinced she'll be paired with her boyfriend Nate, but when she gets paired with his best friend Chuck will Blair get the Valentine's Day she's been waiting for?**

Disclaimer: I do not own Gossip Girl/It Girl or any of it characters

* * *

Blair Waldorf awakened at 7:00A.M on a Monday morning. Normally most kids would groan at the thought of waking up, hit the snooze button and sneak in a couple minutes-maybe hours of sleep. But not Blair Waldorf. And especially not this week.

She removed her sleeping mask and sat up in her Egyptian cotton sheet bed. She stretched her arms out and yawned. This week was the week to get her out of her grouchy state that came along in February. As soon as February hit Blair always got sick of the cold frigid weather. More like exactly when one of her favorite holidays Christmas is over. She would become an even bigger bitch then she usually was. But it usually benefited her because no one went against her at that time of year- unless they wanted to experience social suicide. Or even worse.

Blair pulled away the covers and swung her soft lotion covered legs out of her bed and slid her feet into a pair of slippers. She reached for her black silky robe tossed on her lounge chair and slid it on. She then padded towards her window and pulled away the silk curtains.

Blair basked in the direct sunlight hitting her. It was going to be a great day. Just like what her father would tell her, if your day starts right, it ends right. With Mother Nature on her side, it just seems that she's on the road to a great day-week even.

The significance of this week was simple. It's almost Valentine's Day on the Upper East Side, and what better way to spend it with her boyfriend and finally becoming a woman?

This year's Valentine's Day will be perfect, Blair decided. So last year's Valentine's Day was terrible, but this year would be better. This year she would be spending her Valentine's Day with her boyfriend Nate Archibald, finally doing what they should have done a long time ago.

Blair exited her Audrey Hepburn inspired bedroom and headed on down the spiraling staircase. Dorota greeted her with her usual breakfast which she would barely touch.

"Good morning Miss Blair."

"Good morning Dorota. Isn't it going to be a wonderful day today?"

Dorota puzzled by Blair's newfound happiness set down the tray of yogurt, fruit, croissants, and orange juice.

Blair ignored it and drank the coffee that was already ready for her on the coffee table instead of taking what was set in front of her.

Blair heard her cell phone vibrating on the glass table. She snatched it off the table and scanned the message's contents.

_**Coming over in 20, k?**_

_**-S**_

Blair remembered that she and Serena had planned to walk to school together today and discuss the results.

And by results Blair meant the results for the online personality survey Perfect Match. It was supposed to assign you to your supposed "soul mate." Whether Blair believed in that happening-well she'd have to wait and see. See if the survey would match her with her longtime boyfriend Nate Archibald.

Blair made her way back upstairs to get changed and cleaned up. Being the queen B meant she always had to look her best; not a hair out of place, mismatching buttons-nothing. Blair slid on her Constance uniform and accessorized it to be fit for a queen. With her signature headband and broach in place as well as a bracelet, earrings and not to mention her pink heart ring she always had on her finger. Blair gave a quick once over on her outfit and decided she was ready.

Just as Blair was making her way back downstairs Serena appeared coming from the elevator. She looked radiant as always. Her sunshine golden locks glistened cascading past her slim shoulders her bright smile lighting up the room. Blair envied her I-don't-even-try-to-be-beautiful looks.

"Hey B! Are you ready?"

"As always," Blair replied hoisting her oversized tote bag on her shoulder.

Serena and Blair took the elevator down to the lobby. The strutted down the streets of the Upper East Side when Serena finally brought up the topic to be discussed, "So, aren't you excited to see who you're matched up with?"

"Of course Serena. This survey was just meant to show that Nate and I are meant to be together. Do you think you and Cabbage Patch will be matched up?"

"I don't know to be honest. It would be a whole lot easier if we were but I don't know, we come from different worlds- but a survey shouldn't dictate if a couple should be together or not."

"Yes but it should be an indicator. Serena regardless of whatever feelings you might harbor for Daniel Humphrey it's just not possible for you two to be matched together."

"How can you be so sure you and Nate will be a match?"

"Because Nate and I have been dating forever and we click," so maybe that was a lie. Sure Nate and her weren't clicking for the past while but after Valentine's Day that would be bound to change.

"Whatever you say B. You do know that Penelope wants to be Nate's match right?"

"Please, that's like trading a Prada for a Frada. They will never be matched. I have nothing to worry about from Penelope," Blair stated rolling her eyes.

Serena giggled, "I hope so B."

After a few more minutes of walking and chatting Blair and Serena arrived at Constance. There sitting on the stairs waiting were her minions.

"Hello girls," Blair said condescendingly. She took her place at the top of the stairs looking over her kingdom.

"So how was everyone's weekend?" Blair asked.

There was a lot of mehs and okays. That indicated no gossip to report. Blair sighed inwardly to herself; it was a boring weekend for everyone.

Just then Blair spotted Nate enter the school courtyard alongside with his best friend Chuck Bass. Blair wasn't particularly a fan of Chuck since the first time she met him but started to become friends and partners in crime when it came to scheming. He was the only one that could keep up with her plots and help her with her social destructions. Her minions were okay but not even close to the same caliber as Chuck.

"Hey sweetie," Blair greeted approaching Nate and giving him a peck on the lips completely interrupting what Chuck was saying to Nate.

"Hey. How was your weekend?"

Lonely without you, Blair wanted to say but kept her feelings hidden.

"Waldorf, don't you have any manners?" Chuck interrupted; he had the I-was-standing-here-and-you-haven't-said-anything look.

"Funny you should ask Bass because you clearly don't," Blair retorted a little irritated.

"Ouch, you wound me Waldorf-"

Chuck was cut off by the sound of the bell ringing.

"Let's finish this conversation another time," Chuck finished.

"How about we not," Blair retorted.

"We'll see the next time you need me and begging me for help we'll see if I'll help you."

He has a point, Blair thought, he's the only one she could rely on in the scheming department.

Blair went back to the girls on the steps and Serena and led the way into the school. They were having an assembly first to explain the rules and regulations of this new Perfect Match survey and how it'll work.

Blair's mind drifted as to what will happen once the results are given out. Nate being romantic and finally doing the deed. Blair fantasized what it'd be like but just when it was about to happen she was rudely poked by Serena.

"B aren't you coming?"

"Where?" Blair asked momentarily confused.

"To class silly! Don't you want to know who you'll be paired up with?"

"Oh right," Blair got up and followed Serena to class. She sat at her usual seat in one row from the back of the class seated in the center. She liked being in the middle of everything and being Queen B, she was always in the loop on everything that happened at Constance.

Alphabetically, Mrs. Stanek- her Calculus teacher,- handed out each envelope with the results. It also had a schedule of the events that were scheduled during the week that you must attend with your "mate."

All around Blair could hear cheers, groans and giggling. Blair anxiously awaited to be handed the results. She was so sure she would end up with Nate-what if she ended up with some loser instead?

Finally, Mrs. Stanek gave Serena her sealed envelope and then followed with Blair's. Blair ripped it away from her teacher's hands and was just about to open it but at the corner of her eye she saw Serena opening hers. Blair watched to see who her best friend would get. Blair watched Serena's eyes shift along the paper and watched a frown appear on her perfect features.

"Who did you get?" Blair asked casually.

"Not Dan," Serena sighed. Blair felt a twinge of satisfaction to see Serena not get what she wanted for once.

Blair then tore the envelope open unable to wait any longer. She unfolded the papers and got to the one with the results. She scanned the content of the paper and felt her stomach drop and the breath be knocked out of her. There's no way, Blair thought inwardly to herself. Blair noticed she was shaking and composed herself trying not to show the slightest bit of emotion. Blair's perfect match wasn't with her beloved Nate.

Blair's perfect match was none other than the womanizing pig, Chuck Bass.

_**Oh my how the mighty have fallen. Poor B, what she hoped would be her white knight being her perfect match was clearly mistaken for the devil. Hm, the Queen B and the devil? Now that's a couple worth rooting for.**_

_**XOXO Gossip Girl **_

_**

* * *

**_

A/N: So? What did you think? Should I continue? Thoughts? Opinions? Review!


	2. Two

A/N: Wow thanks for all the reviews guys! Seriously to any writer on here it means a lot! I was going to update all during the week but I was away for a couple days and didn't have time. Anyways here's the next chapter! Enjoy and review please!

Disclaimer: I do not own Gossip Girl or any of its characters

* * *

Blair bolted out of her seat as soon as the bell rang to the start of lunch. She ignored Serena's calls coming from behind her and angrily twisted the lock and its combination. She felt tears threating prickling her eyes from humiliation. She was so sure she'd be with Nate. Positive.

The Perfect Match survey must have made a mistake. That, or Nate didn't fill out the survey. Blair immediately ruled out the second option because Nate told her he did and he wouldn't lie to her. Okay so maybe he did once with his fling with Serena but that's it. She should be forgiving to him.

"B, what's wrong? You practically sprinted from that room and probably set a world record," Serena spoke catching her breath.

"Nothing is wrong Serena," Blair snapped. Blair shoved her books in the locker and slammed the door.

"Defiantly not," Serena mumbled.

"B, is this about the survey?" Serena didn't need an answer to know the answer, "You weren't matched with Nate were you?" Serena paused, "Who were you matched with?"

Blair sighed defeated, "Chuck," she answered quietly.

"Chuck?" Serena said in surprise, "Oh… well it could be worse-"

"How could it be worse Serena? It's Chuck Fricking Bass!" Blair hissed in low tones so no one would hear.

"Well at least you're friends with him."

Blair rolled her eyes, "Yes and he's also a rapist."

"Don't be so dramatic B, this isn't the end of the world."

"Oh really? I told Chuck that I'd only ever be with him when hell froze over; if you look around Serena, there's no ice!" Not to mention it would ruin her perfectly planned Valentine's Day.

"Well there's nothing you can do now B."

"Oh there's plenty I could do. I could-"

Serena raised her palm," I'm not interested in hearing this. Come on B, the girls are waiting to go and have lunch on the steps."

"Fine. We could ditch them if we wanted; they're only minions you know."

"Yes but if I remember correctly you promised to have lunch with them. If I remember correctly as Queen you must fulfill your duties."

Blair and Serena approached the courtyard. All of Blair's minions sat at one of the stone picnic tables waiting patiently, and gossiping. Blair figured Gossip Girl had sent out a blast. Great, that's just what she needed to fuel this disaster.

Blair approached her minions, Serena by her side, "Hello girls, are we ready for lunch?"

"At the steps?" Penelope asked.

"Where else Penelope? Did that party last weekend kill the last of your brain cells?" Blair snapped.

Penelope sat there verbally slapped by her queen. Anger was evident in her facial expression but Blair had nothing to fear. Blair knew every one of Penelope's dirty little secrets and knew she was nowhere near capable of a queen takedown.

"Let's go girls," Blair commanded leading the way out of the school. Blair turned around to make sure everyone was behind her. Blair stopped to see that Penelope didn't budge.

"You coming Penelope?" Blair asked reluctantly. Seriously what was her problem?

"Yeah," She finally got up and followed the girls of the steps.

The girls arrived at the steps and took their spots Blair taking hers at the top of the group.

Blair opened up her yogurt and spooned a mouthful into her mouth. Her stomach greatly appreciated the nutrients as Blair kept eating.

"So Blair did you hear who Hazel got?"

"Who's the lucky guy Hazel?"

"Do you remember that Spanish exchange student?"

"Wait you got him while I'm stuck with Andy Clark!" Penelope interjected with frustration.

"Very nice Hazel," Blair spoke with approval.

"So Blair did you get matched up with Nate?" Iz asked.

"No actually," Blair replied with honestly. She might as well tell them the truth now because it will for sure end up on Gossip Girl soon anyway.

"Who then?" Penelope asked her eyebrows rose waiting to hear the details.

Blair's throat locked. Her lips formed a thin line but she showed no emotion or weakness, "Chuck Bass."

"Oh my god," Hazel said. Blair shot her a death look which shut her up quickly.

"It's the infamous Chuck Bass B. I'd be careful if I were you," Iz warned.

"You have nothing to worry about Iz, unlike all of you which he's probably slept with he'd never lay a hand on me. I have nothing to worry about. At least I know my date," Blair took another shot at Penelope.

"It's only a stupid survey anyway," Blair concluded.

Serena who had been silent this whole time was finally brought in the conversation," Hey Serena who is your match?" Hazel asked.

"It's not from Brooklyn right?" Iz asked.

"No," Serena answered giving away no more than a one word answer.

"You didn't tell me before, who did you get paired with Serena?" Blair chimed in.

Just as Serena opened her mouth to answer everyone's phone started ringing.

"Gossip Girl," Blair said knowingly.

_**Hell hath no fury like a Blair Waldorf scorned. Careful S, when being matched with the queen's king there are bound to be consequences. Looks like a little reunion is just around the corner… **_

_**Xoxo Gossip Girl**_

Blair looked up from her phone and looked directly at Serena. No words could express this betrayal. She took Nate again.

"I'm so sorry B, it was out of my control."

She always took everything that was mine. Everything. She took Nate from me once already. But now a second? Blair thought angrily.

No one said a word as Blair felt a battle between her emotions inside her at that very moment.

Blair kept her composure and finally spoke up, "Serena I'm going to have to ask you to please leave. Now."

"But B-"

"I said go," Blair cut her off icily.

Serena taken aback from Blair's request-make that order-stood, "fine," she replied only above a whisper.

Serena walked away and no one said a word. No one wanted to be on Blair's bad side. It was social suicide.

"Come on girls we'll be late for class," Blair stated as soon as Serena was out of sight.

Blair and her minions arrived back at Constance. They all parted in different directions as Blair approached her locker the last person she wanted to see appeared.

"Waldorf- Or should I say Match?"

Blair rolled her eyes, now was not the time for this, "Keep it to Waldorf."

"Alright Match."

"Bass I just politely asked you not to call me that. Are you suffering from short term memory loss?" She knew he was just doing it to get a rise out of her. And it was working.

"No but you're not exactly being the most welcoming either. You know you should be grateful to be matched with me, most girls would be."

Blair rolled her eyes, "Don't flatter yourself. Clearly this thing is wrong because I should be matched with-"

"Nate? Oh I hate to break it to you but he's matched with Serena."

"Thanks for the reminder Bass. Like I didn't know already."

"No problem. So what are we supposed to do for this match thing anyway?"

"Where were you Bass during the assembly?"

Chuck gave her a class Bass look that screamed you-know-perfectly-well-that-I-don't-care-about-school, look.

"I was with your dear Nathaniel, anyways fill me in."

"Well there are a few activities this week you must attend with your match."

"Which would be?"

"Tonight is movie night. They're showing Casablanca. There's a carnival all day Wednesday and lastly there is the Valentine's Day Ball on Valentine's day. By next week everyone is expected to write a paper about the experience and it'll be worth marks so regrettably, everyone has to participate."

"See, you wonder why I don't show up for assemblies, I can just get the bullet version from you."

Blair rolled her eyes, "Yes but what if one day I'm not here. What will you do then?"

"Nothing, come on Waldorf, you know I don't care about school."

"Nope I was completely oblivious to that," Blair retorted sarcastically.

Chuck smirked, "What would I do without you Waldorf. There'd be no one to challenge me with their wit."

"You'd be very bored wouldn't you Bass?" Blair smirked in response.

"Yes I would be, but I'd find other ways to entertain myself-"

"Alright I don't need to hear any of Chuck Basses escapades thank you very much," Blair interrupted.

Chuck smirked, "So is the movie being played at the school?" Chuck asked changing the subject.

"Yes and don't even think of bailing on me Bass. We are required to go. It's practically mandatory."

"Stand up Queen B? Wouldn't dream of it. I'll see you tonight Match," Chuck concluded and started walking in the opposite direction.

"Unfortunately," Blair added under her breath. Blair caught Chuck looking back at her.

"Sassy Blair. I like it."

"Keep walking Bass."

* * *

A/N: So what did you think? Review please!


	3. Three

A/N: Thanks for the reviews guys! I can't tell you enough how much they mean to me! Anyways here's the next chapter!

Disclaimer: I do not own Gossip Girl or the It girl series.

* * *

Blair gave one more look over her outfit that night before exiting her bedroom. Tonight was movie night and Blair wanted to avoid it like the plague. However, if she wanted to get into Yale she'd have to participate, so she could write up her paper and not fail that portion of this whole simulation. Simply Blair would have loved to make up something, but they are recording attendance and Blair reluctantly was attending.

Blair arrived at the school, signed in her name and made her way into the auditorium. The school auditorium assumed its movie style seats would work perfectly for the event as well as the projector screen that descended from above the stage.

Normally Blair would make her entrance with her minions; however they choose to come with their dates. And of course Chuck Bass would never escort her to an event, he's Chuck Bass. Enough said.

Blair's eyes scanned over the rows of seats to find her minions as well as Serena and Nate. Since the movie hadn't started yet, the lights had yet to be dimmed. Blair spotted her minions in a clump with their dates accompanying them. Iz waved at her to come and join them. Blair started coming up the stairs when she spotted Serena. With Nate.

Blair could barely contain the anger inside of her. Her Nate with her cheating best friend. Serena and Nate were laughing near the top left corner of the auditorium. Blair's heart sank to see them having fun together. Nate was supposed to love her not Serena; but of course Serena was better than her. She always was to everyone and always will be, Blair concluded.

Blair took a seat beside Iz without her date. She actually hadn't seen Chuck at all and wasn't surprised that he didn't show. Typical Bass.

The movie started with the opening credits and the title _Casablanca _appeared. Personally, Blair would have preferred an Audrey movie any day but she'd settle. It's not like she didn't like Casablanca. It's just well; it just wasn't a movie with Audrey.

This is pointless, Blair thought to herself bitterly. The whole point of coming tonight was to spend time with her match, but of course he didn't show. All of the men in Blair's life have bailed. Her father, Nate… Blair always thought Chuck was on her side, he was always there for her-but now…

She contemplated leaving. She casually looked over her shoulder to see Nate whispering something to Serena and she giggled in response. Blair whipped her head back around to the screen before one of them saw her looking. She could hear Serena's four year old laugh echo through the theatre.

Okay maybe she was imaging that part. Blair looked back again to see Serena slap Nate playfully on the shoulder. Blair turned her head back again and felt her heart sink.

Standing up, Blair picked up her purse and before she stood to leave. She couldn't take their open flirtation anymore.

"Where are you going?"Iz whispered.

"The bathroom, I'll be back," Blair whispered back.

Blair was just making her way to the exit when someone blocked her escape.

"Waldorf isn't it a little early to be leaving? The movie just started."

"It isn't when your date stands you up, Chuck" Blair snapped.

"Ouch, alright so I was a little late on getting here but Andrea was so-"

"That's already too much information Bass," Blair interrupted. She just wanted to leave and of course now would be the time he decided to show up.

"Waldorf listen I'm here now aren't I? Let's just go sit down and watch this stupid movie."

"No thanks I was just going to leave."

Blair stepped to her left trying to maneuver her way around Chuck. But as soon as she stepped left, he stepped to his right still blocking her path. Blair becoming more frustrated moved to the right and Chuck still posing as a roadblock.

"Bass do you mind?"

"Yes, yes I do," Chuck responded. Blair could tell he was enjoying this.

"For someone who is so concerned about getting into Yale, I didn't see you as breaking the rules type Waldorf."

"Well I signed in already so I technically am not so move Bass!" Blair hissed.

"On one condition."

"No," Blair responded assuming he meant something sexual.

"No not that Blair, but thanks for assuming that."

"Sorry," Blair apologized noticing Chuck was a little hurt-only a little. "What is the condition?"

"That I come with you. These people bore me at school."

Never in a million years did Blair ever think Chuck would have said that. So he wanted to spend time with her? That just seemed so unlike Chuck.

"Well, all I was going to do is go home so it's not that exciting."

"It can be, plot to socially destruct someone, watch Tiffany's like you made us when we were little."

Blair thought for a minute lips pursed, "Fine. Condition granted."

"Well then," Chuck offered his arm to her, "Waldorf."

"You're pushing it Bass," Blair pasted her bitch smile on her face and started walking out of the auditorium. Chuck smirked and followed her out of school and into his awaiting limo.

"To the Waldorf Penthouse, Arthur" Chuck commanded his driver.

Blair had to admit, Chuck's limo was amazing. Her mother always told her to take a cab or walk to school. Blair preferred it better that way. She felt like Audrey calling for a taxi in Tiffany's and if she ever needed a ride Chuck always gave her one.

Shortly after an uneventful ride in the limo, Chuck and Blair entered the penthouse to be greeted by Dorota.

"Hello Mrs. Blair, Mr. Chuck."

"Hi Dorota," Blair greeted her maid.

"I take coat yes?"

"Yes that would be lovely Dorota," Chuck handed the maid his Armani coat, "Thank you."

Blair turned to him and finally asked, "Why are you being so nice to me?"

Chuck chuckled, "Whatever do you mean?"

"It's just usually you'd have better things to do then come to a school event."

"The only reason I came is because you asked me Blair. Come to think of it, you kind of threatened me," Chuck joked.

"Well thanks. And now since you're here I'm taking you up to that Tiffany's offer," Blair said making her way to the stairs. It's been awhile for Tiffany's and after seeing Nate and Serena together, it's just what she needed.

"You wanted to come so this is what we are going to do. Okay?" Blair stated starting to walk up the winding staircase.

"Sure."

Blair looked at him in disbelief.

"What?" Chuck asked as he came up behind her.

Blair looked over her shoulder," nothing, it's just you never have given in to watching Tiffany's that easily. I was expecting a groan and 'do we have to Waldorf?'" She imitated him.

Chuck smirked walking up behind her, "Well, it's been awhile since I've seen it, and I did suggest it. Regrettably."

Blair and Chuck finished climbing the staircase and arrived in Blair's bedroom. Blair picked out the DVD case, and popped it into the DVD player. Blair flicked onto the play button and walked over to her bed where Chuck was already sitting. It was just like old times.

"If it was always this easy to get you in bed," Chuck remarked.

Blair rolled her eyes, "It will never be again Bass, so don't even worry about it," Blair retorted.

She turned to see him smirking back at her.

The opening credits finish rolling and in comes Audrey eating breakfast; at Tiffany's. Blair's mind wandered to Nate and how much fun he was having with Serena until a light bulb flashed brightly in Blair's head.

Now would be the perfect time to ask about Nate. Who better than his best friend for over ten years?

"So Chuck," Blair started casually, "Has your best friend mention anything about his perfect match?" Blair asked innocently.

"Nothing, and if you are referring to him being matched with your best friend, he has said nothing. Waldorf, you have nothing to worry about with Serena. Just trust Nate."

"It's kind of hard to when he has been unfaithful before," Blair bit out.

"True, but you forgave him so now you'll have to deal with the paranoia of him possibly cheating on you again."

Blair was startled by how right Chuck was," How would you know Chuck? You're not exactly the relationship type," Blair smirked.

"Yes but having seen enough couples over the years either be blissfully happy or self-destruct, I know a relationship is way overrated."

"No it isn't Bass. You just don't like being committed. Or maybe," Blair spoke pointing her index finger to his chest," You have a fear of it."

"You're delusional Waldorf. All this love garbage is going to your head. Stop trying to change the subject. I thought we were talking about Nate?"

"Love is not garbage! You don't even know what love is!" Blair replied defensively. This is why Chuck Bass doesn't have friends, Blair thought to herself. It's difficult just having a conversation with him. How irritating.

"Whatever, Waldorf. Just go on believing what you want to believe."

Silence filled the room and only Audrey's voice emitted any sound in the otherwise awkward silence.

"So are you sure Nate hasn't said anything about Serena?" Blair asked quietly her insecurities showing slightly.

"Nothing why are you so worried?"

Blair contemplated telling him the true reason; everyone liked Serena more than her. Serena always was better, prettier, nicer… the list goes on.

"Like I said, Nate cheated on me once. I just want to make sure he doesn't again."

"He won't. Well," The words died off of Chuck's tongue realizing he couldn't be too sure with Nate.

"If he does, then I'll hire someone to beat his ass. How does that sound?"

Blair pictured Nate with two black eyes and fat lip and bloody nose. She would never want to see him hurt. But then the vision of Nate and Serena laughing together, Nate and Serena kissing each other Nate and Serena- Blair shrugged the last thought away and then the idea didn't sound so bad.

"Sounds perfect."

They both focused their attention back to the movie and Blair started to feel her eyes droop to a close.

Blair opened her eyes to find herself alone, in her bedroom in the dark. Blair flicked on her bedside lamp and let her eyes adjust to the brightness. She was tucked into bed with the clothes she wore to the movie night on.

Where did Chuck go? Blair glanced at the clock on her bed stand. It was almost two in the morning. I must have fallen asleep while watching the movie, Blair thought to herself.

Chuck must have left before the movie was over-wait he most defiantly did. He wouldn't have stayed where his date fell asleep on him. This is Chuck Bass we're talking about here.

Blair looked at her attire surprised that he didn't take this opportunity to undress her. But then again, Blair knew Chuck respected her more than that which Blair appreciated.

Blair stood and padded over to her closet. She sleepily put on her sleeping garments and went back to bed. She shut off the light wondering maybe Chuck Bass was human after all.

_**Well Upper East Siders, I must say aside from the seemingly mismatched and peculiar pairings maybe this Perfect Match has some truth to it. I mean S and N? D and Y? And not to mention to most shocking of all C and B. Spotted: B fleeing movie night early being escorted by C. Looks like the Queen B is being lured to the dark side. Careful B…**_

_**Xoxo, Gossip Girl**_

_**

* * *

**_

__A/N: What did you think? Please leave me a review!


	4. Four

A/N: Thanks for all the reviews guys! Sorry I haven't been able to update at all this week but school was absolutly insane! Anyway here is the next chapter! Please review!

Disclaimer: I do not own Gossip Girl OR the It Girl Series

* * *

Four

The next morning Blair opened the door and stepped out of the classic New York yellow taxi. She paid the driver and gathered her possessions. She slung her large tote over her shoulder and slammed the door behind her. She turned facing Constance and took a deep breath out of the winter air.

She decided to make the best of this situation. Sure, she didn't get matched with Nate, but Blair was going to trust him and make the best of it with Chuck. He was one of her closest friends after all.

Blair strolled into Constance looking for Nate. She barely saw him yesterday and she had something she wanted to tell him-Well hint.

Okay, so maybe she was a little uneasy about how much time he spent with Serena yesterday; but she'll be reassured once she talks to him, Blair was sure of it.

Blair scaned the crowds of students. Finally she spotted Nate and approached him. Blair quickly paced up the staircase.

"Hey sweetie," Blair pecked Nate's lips, "I didn't have a chance to talk much with you yesterday. How are you?"

"Oh you know, I'm fine. Just been busy."

Blair started to walk alongside Nate her arm linked to his, and nodded. Just busy? What kind of excuse was that?

"You know Blair about this Match thing," Nate continued, "I don't want you to feel awkward with me being matched with Serena and considering everything that's happened, because I told you I love you and carry no feeling for Serena."

"I know silly," Blair spoke brightening at him telling her he loved her. "I love you too. And I trust you Nate."

Nate flashed his perfect smile, "I knew you would." Nate pecked her ruby lips and Blair smiled. See? Nothing to worry about.

"So," Blair fiddled with the hem of Nate's coat, "There's been something that I've wanted to do for a long time you know?" Blair threaded her arms around his neck, "Find me after the Ball this Friday because I have a little… surprise for you," Blair kissed him passionately a smug smile tugging at her lips.

"Okay," Nate replied dazed, kissing her again. Blair pulled back her arms and turned away to see Chuck Bass standing at the doorway to Constance side of the courtyard.

"Must you display your affections for each other in front of all to see? It's nauseating," Chuck said with a disgusted look on his face.

"Please, most people would prefer to see that then you with your conquests or even worse victims," Blair retorted.

Chuck smirked. "I guess I'm just not used to my dates falling asleep on me."

Blair rolled her eyes, "Sorry, but I was tired. Guess all those rumors about you aren't true after all."

"Care to enlighten me with those rumors?"

"Nope. Any more boasts to your ego and your head might explode."

Chuck laughed, "That's a good one Waldorf, and I'll admit that."

Blair smiled in satisfaction. "Thanks by the way. For last night."

"Oh please, anyone wouldn't pass up the opportunity to spend time with the Queen B. Especially in her sacred untouched bedroom," Chuck smirked.

"Must you make everything into something sexual?"

"Why? Does it bother you?" Chuck asked.

"Slightly."

"Then of course," Blair elbowed him playfully in his ribs.

They arrived at Blair's locker and Blair twisted the combination into her lock. She snapped it open and swung open the wooden locker door.

"So what is on the agenda this evening?"

"What do you mean?" Blair asked.

"As I recall you said we were supposed to spend time with our matches every day this week. So what are we going to do? Oh, and please don't make me suffer through another Audrey movie. You can barely stay awake through them yourself," Chuck smirked.

Blair rolled her eyes, "That was only one time Chuck."

"So what are we doing?"

"I don't know. I might have asked you but then I wouldn't want to subject myself to anything you'd want to do. "

"Why do you always assume that I always want to do something like that?"

"Forgive me for all your sexual innuendos, and come-ons."

"Yes but what else do you think I like from what I told you?"

Blair took a minute and thought about it. Sure Chuck's image consisted of drinking, womanizing, drugs, social destruction. But what else? I've known Chuck for forever and I don't even know what he likes? Blair thought to herself.

"Exactly," Chuck stated proving his point.

"Well what else do you like then?" Blair asked.

"Sports-"

"Pssh, you sports Bass? I never thought you did anything athletic besides removing your scarf."

Chuck gave her a no-judging-look, "Okay," Blair conceded, "what sports do you like?" Blair asked.

"A little bit of everything I guess. Except wrestling and such- Unless it's with girls." Chuck smirked.

Blair gave him a disgusted look, "You're disgusting."

"I'm just joking Waldorf."

"Well, do you have a favorite?"

"I do enjoy squash. And I beat my dad in the eighth grade which I never let him forget."

"That shouldn't have been too hard to beat your dad," Blair replied.

"Oh believe me- my dad is extremely competitive and extremely fit for his age- It's a wonder I beat him in grade eight."

"Wow, quite the accomplishment," Blair stated sarcastically.

"Don't even Waldorf. You probably have never played in your life. It takes a lot of hand eye coordination."

"Yes I have," Blair responded.

"Really?" Chuck asked skeptically.

"Why are you so surprised?" Blair questioned pulling out her math textbook and binder.

"I just never expected you to play many sports Waldorf."

"Neither do you," Blair retorted, then she suddenly came up with an idea, "I know, why don't have a game of squash tonight Bass?"

"Squash? That's what you want to do?"

"Why not? I haven't played for a while it should be fun," Blair answered grabbing for her pencil case.

"Okay Waldorf, whatever you want, but don't be ashamed if I win."

"Excuse me? Aren't you being a little over confident?"

"No I'm just saying don't feel too bad. Just give it your best shot so to speak."

"Uh huh, well see about that Bass." Blair shut her locker door closed. Blair felt fueled up for this competition with Chuck. It is so on.

Later after lunch Blair met with the minions to go for lunch. They decided on a new place called Martinis for lunch.

After everyone had ordered what they wanted to eat all her minions started gossiping about all the matches.

"Andy isn't that bad after all," Penelope boosted.

"Please, anything that walks on two legs isn't that bad for you Penelope," Blair said getting annoyed with her. Penelope never knew when to stop. It was every once and a… well couple days she would remind her to stop.

"Fernando is so dreamy. We're going for dinner and said he was going to leave a surprise after!" Hazel spoke giddily.

Blair rolled her eyes, "What are we twelve? Hazel shouldn't you know that when a guy says he has a surprise it isn't one. He just wants some action."

"Yes, but so do I," Hazel replied honestly.

"Blair where were you last night? One minute you were beside us the next you were gone," Penelope asked. She defiantly could tell something fishy was going on.

"I was feeling sick so I went home," Blair lied. She wouldn't give Penelope or the rest the satisfaction let alone the truth. They don't need to know everything that their queen does.

"So do you have any plans with Chuck tonight?"

The server came with everyone's main course. Blair eyed her salad hungrily. She took a few small bites and answered the question," I'm not sure yet, I haven't had a chance to talk to him today."

"I thought I saw Chuck at your locker today B?"Iz question curiously. Shit, Blair cursed in her head.

"Well we were just discussing something else and didn't have a chance to talk about any plans tonight."

Blair took maybe twelve bites then put her fork down in its five o'clock position on her plate. The chatter continued on and thankfully the spotlight was off of her. Blair thought about the competition that she and Chuck had. The fact that he is underestimating Blair is a big mistake. Blair was more determined than ever to beat him just to prove him wrong. And also rubbing it in his face wouldn't be a bad thing either.

"B?" Blair snapped out of her thoughts when Iz was calling her attention. "Are you ready to pay and go back to school?"

All her minions awaited her final say to follow her orders. That's what Blair loved about her power. Everyone did what she told them too and she had control.

"Yes, let's go."

Later that night, Chuck came to pick up Blair for their little game. Blair had on spandex short shorts underneath her yoga pants. With a pink sweater and polo underneath. Normally she would NEVER be dressed down so severely but this was purely for athletic purposes so she made an exception.

Blair exited the Waldorf penthouse to see Chuck's awaiting limo. Arthur stood outside of it and opened the door for her to climb in.

"Thank you," Blair mentioned politely and slide across the black premium leather seats.

"Waldorf, good to see you again."

"As much as it pains me to say it you too," Blair replied.

"I'm so touched," Chuck said sarcastically.

Blair studied Chuck's attire. He wore a yellow headband around his forehead, and had on navy blue shorts with a navy blue shirt with the design of gold and silver crowns. He also wore a sports jacket, which remained unzipped and his face holding a smirk. In essence, it was completely Chuck Bass.

Shortly Chuck and Blair arrived at the sporting arena. Of course being Chuck Bass, he had a squash court booked and everything. There was a girls and boys change room. Blair entered the girls change room to see walls of blue half lockers and a long bend going down the middle. She picked a locker and opened it taking the key and keeping it with her and shed her yoga pants and sweater. She closed the locker and exited to be with a greeted with a waiting Chuck.

Chuck scanned her up and down and Blair felt herself blush. Maybe she should have kept the yoga pants on. They probably were more flattering.

"I am for once going to restrain myself form saying something I usually would say. You look really good Waldorf," Chuck complimented.

"Thanks Bass," Blair said, her confidence restored. "Let's play."

* * *

"Wait? What's that? Oh yes I won Chuck!" Blair exclaimed smiling. Her face was glistening with sweat and felt disgusting but it was totally worth it.

"I was having an off day Waldorf," Chuck retorted defensively.

"Uh huh, or you could just admit that I beat you!" Blair gloated happily.

"For the record no one will know about this are we clear?"

Blair waltzed to the girls change room suddenly whipping her head back to him, "Not going to happen Bass. If you won, you would have said it to everyone. Why can't I do the same?" Blair turned back around cleaned herself up and gathered up all her things and came back out.

"Fine…you won okay?" Chuck stated humbly. He had to admit and give credit to her, even if he lost.

"Yes I did thank you fair and square-"

"That second last point was out of bounds!" Chuck argued.

They made their way out to the limo waiting at the curb which Chuck opened the door for her and let her in first and got in himself.

"It was not out of bounds get over it! I won and the only thing that got squashed tonight was your humongous ego Chuck."

Chuck didn't say anything but starred out the window. A silence took over and the playful mood turned sour.

"Are you going to be mad that you lost now?"

"No I'm actually just a little tired. And I think I may have pulled a few muscles."

Blair giggled," There's a thing called stretching before you exercise Chuck."

"Thank you I'll keep that in mind for next time," Chuck retorted.

"Well surprisingly I did have a good time tonight-not just because I won by the way."

"All girls have a good time with Chuck Bass," Chuck smirked.

"And the ego is back," Blair rolled her eyes.

"Well aside from losing I had a good time as well Waldorf."

The limo jolted to a stop in front of the Waldorf penthouse, "Well thank you for this evening Chuck."

Chuck opened the door and let Blair get out," Anytime Waldorf."

Blair just nodded her head and started to walk into the building until she heard Chuck call out to her, "What no goodbye kiss?"

Blair turned around and smiled, "For you," then she finished her thought with seriousness, "No."

With that, Blair slammed the door in his face turned around sharply and started walking back to her home. Blair smirked and but a little more swagger into her step being quite aware that Chuck was watching her every step. And maybe deep, deep down inside she kind of liked it.

_**Spotted: Queen B being dropped off by C from a mystery destination. A mystery date perhaps? Meanwhile D and Y discussing nineteenth century literature at a Brooklyn coffee shop. How boring. The most puzzling of all is not one sighting of S and N. Wonder what they're up too…**_

_**XOXO Gossip Girl**_

_**

* * *

**_

A/N: I should also clarify that Y stands for Nelly Yuki. I didn't want people to get confused because Nate also has the same initials. I also figured Blair dosen't win enough on the show and a victory here would be quite fitting. Anyways, please review!


	5. Five

A/N: Thanks again for all the wonderful reviews! You guys are amazing!

Disclaimer: I do not own Gossip Girl or any of its characters

* * *

The next morning Blair strolled to school the warming spring weather all around her. The sun was shining, the trees were blooming. It just _smelled_ like spring. Everything was coming back to life, and in a sense so was Blair.

In truth, Blair's mood had indeed improved from a couple days ago. After the end of this week, we it'll be even better she thought. Blair felt a cool breeze whip her cheeks, causing them to become rosy. Blair didn't mind at all.

Blair entered the school's open gates to see her minions in their rightful places; as per usual. Today, as Blair recalled was the carnival. It was a part of the perfect match simulation and Blair didn't know what to expect. Was there going to be people on stilts? Rides? Or even clowns?

Blair looked around to see many pin striped tents set up all around with different games and activities and food. Well it sure beats classes, Blair thought to herself as she approached her minions.

All three of them plus little Jenny Humphrey stood at the top of the stairs eating their yogurts while waiting for their queen.

"Good morning girls," Blair readjusted her large tote bag on her shoulder.

All the girls gave their greeting to their queen.

"Are you girls excited for the carnival?" Blair asked all of them.

"Totally, I love cotton candy and I just spotted a tent over there," little J pointed out excitedly behind Blair.

"This is going to be lame," Hazel complained. "A carnival? What are we twelve?"

"Oh- your right I guess," Jenny mumbled to her superiors.

Blair cocked her head in Jenny's direction, "No Jenny. This can be fun. Carnivals have a mysterious air to them."

Jenny smiled gratefully to Blair while Hazel scowled. Blair shot her a cold look which caused Hazel to change her mood.

"What's wrong Hazel? No action with Fernando last night?" Blair asked innocently.

Hazel's cheeks flushed bright red which notified Blair with the answer.

"What did you end up doing with Chuck last night B? Did your V-Card get swiped finally?" Penelope pipped up.

"For your information Penelope my sex life is none of your business. However to answer your question which you'll never ask again, no my V-card is unused which is something I can't say for you. I think yours is close to being maxed out," Blair said wickedly. Blair smiled and batted her eyes back to Penelope innocently as Penelope stood as still as a statue.

"Now, as much as I'd like to know about how all your dates went last night, it's almost time for us to find our matches and attend this carnival. I'll text you all what we'll be doing later."

Blair spun on her heels and walked towards the Constance building where Chuck was leaning in the doorway as if he were waiting for her.

"Bass."

"Waldorf, always a pleasure," Chuck flashed his classic Bass smirk to her.

Blair found herself smiling, "Even after I beat you last night?" Blair moved past Chuck through the doorway and into the hallway going to her locker. Chuck walked alongside her, "So maybe my ego was a little bruised, however my other attributes make up for it. Other skills I have that would beat your inexperienced self."

"Well some of us respect ourselves and our bodies to not have those skills. But how would you know?"

"You've barely gone to second base with dear Nathaniel; I think that speaks for itself."

"I will be experienced by the end of this week thank you, not that it's any of your business," Blair and Chuck arrived at Blair's locker and Blair opened it tossing her bag and books into it.

"Why don't you become experienced right now?"

"Ew, you're heinous Bass," Blair replied disgusted.

"True, but I did get matched to you so you'll have to live with it won't you?"

"I only will for the remainder of the week. After that everything will be normal again, thank god," Blair shut the dark wooden door closed and snapped her lock back on.

"Now what are we supposed to do?" Chuck asked.

"Well since it is Wednesday, it is the day of the carnival for this Perfect Match thing. Basically we have a carnival style event set up all around school with food stations, games and activities if you haven't noticed."

"What are we the middle class?" Chuck asked disgusted.

"Obviously not, but we have to attend-"

"Why is it always Waldorf that you insist on following the rules?"

"Because Yale is on the line! I'm not wanting to risk Yale for a stupid mistake I made with you. So deal with it. What else do you have better to do?"

"Well for your information I am a busy person you know," Chuck said a matter-of-factly.

"Oh really? What important things does Chuck Bass do?" Blair started walking towards the courtyard which Chuck by her side, "Let's see there's drinking, smoking pot, womanizing, skipping school-"

"Waldorf that's not what I meant. I actually do take some things seriously," Chuck replied defensively.

"Like what?" Blair questioned not believing him.

"Well…" Chuck stopped himself from continuing what he was going to say.

"Tell me Chuck," Blair prodded. What was he not telling her?

"Well, there is this property I found. I-I well over the past few weeks I have put together a business proposal for my dad to see if he'll buy it and maybe I'll be in charge of it. I wanted you to come see it first before I present it to him."

Blair was completely taken aback. Chuck Bass is actually doing something with his life?

"What? You don't believe me do you," Chuck said from the lack of response from Blair.

"No- Chuck that's fantastic! I just-I didn't know you wanted to follow your dad in the business path."

"Well most people expect me to take it over anyways."

"You don't have to if you don't want to. I mean everyone expects everything that our parents did from us and more, if we don't want to do it we shouldn't have to. But I think you'd be a great businessman Chuck."

"This is coming from the girl that is destined to marry an Archibald, go to Yale and have a perfect little family," Chuck stated ironically, "Now you're starting to sound like Nathaniel."

Blair wanted to ask what he meant about that but kept her mouth shut. Save it for another day.

"So Blair, will you come with me tomorrow morning to check out the place before I make the business proposal to my father?"

"Of course," Blair said in a heat beat. She knew this meant the world to Chuck and she'd defiantly be there to support him. And by the look on Chuck's relieved face she was doing the right thing.

Blair looked around to see a few games set up at a few of the tents, "So for the task at hand. How about we play one of those games?" Blair pointed to a yellow and red pin striped tent that had the game with a table displaying big green glass bottles lined up row upon row. The worker running the tent held a bucket full of rings for everyone to try to throw one and land perfectly around the neck of a bottle.

"Do you think your ego can handle losing again?" Blair taunted motioning towards the stand.

"I never lose Waldorf," Chuck stated.

"Then what happened last night?"

"I let you win," Chuck said.

"Whatever Bass. I won fair and square. You even admitted it to me."

"I only said it so you would shut up about winning."

"Really? Well how about this time we play this game," Blair pointed to the whack-a-mole game instead of the bottle game knowing she has always won at that game.

"And," She continued, "this time you can't use the excuse that you let me win this time. Got it?"

"You're so on Waldorf."

Chuck and Blair approached the tent and each took a whack a mole station. The machine counted down to zero until the game started. Blair quick as a cheetah, smashed the moles with the whacker with all her might. She just pretended it was Penelope, Serena and even Chuck for that matter. His egotistical face.

Blair punched and obliterated the moles vigorously with all her might. She wasn't even paying attention to what Chuck was doing she wanted to win so badly.

The timer went off signaling the end of the game and Blair looked up to see that she was the winner, "I won! That's two for two Bass!"

"Fine you won this time but how about," Chuck looked at the stations around for another challenge," we play that game and winner takes all."

"Fine, I'll beat you again!" Blair replied confidently.

Blair noticed it was the same station with the bottles and rings. Crap. Maybe she shouldn't have agreed to this. Blair knew she wasn't very good at this game.

They were both handed five rings. "Ladies first," Chuck smirked at her.

Blair threw her first toss. It bounced off the cap of the one bottle but fell in between two nearby green bottles.

Chuck then made his first toss. He nicked the corner of the cap of the bottle barely missing. "So close," he said after.

After a couple of tosses by both of them Chuck and Blair had little success. Chuck took his second last turn. He tossed the ring which bounced off one green bottle and the ring secured itself around another green bottle beside it. Chuck had won.

"That's right Waldorf! Who's the winner now?" Chuck was handed a stuffed animal that looked like the Yale bulldog.

"Good job," Blair forced out, her competitive edge unsatisfied of the loss.

"Thank you Waldorf. Here take this," Chuck handed her the stuffed animal he'd won.

"Chuck you won fair and square-"

"Just accept the gift Waldorf will you? Besides, Chuck Bass doesn't own stuffed animals."

Blair smiled and Chuck handed it to her.

"It looks like the Yale Bulldog doesn't it?" Chuck said.

"It does. Thanks Chuck," Blair said grinning from ear to ear. Since when did Chuck Bass ever do anything nice for anyone?

Chuck cracked a little smile to her- barely there but she saw it. Come to think of it Chuck usually never smiles, Blair pondered. Blair's thoughts were yanked away when someone called her name disturbing the moment.

"Hey B."

Blair whipped her head around, her chestnut curls cascading around her face. Her eyes met with Serena's and knew she wanted to talk.

Blair turned her head back around to Chuck giving him a look saying can we have a minute?

Chuck understood immediately," I think I left something in my locker."

Blair met with Serena face to face.

"B, I haven't talked to you in days. How are you?"

"Fine," Blair replied curtly.

Serena could sense Blair's coldness as she apologized," Blair I'm sorry that I got matched up with Nate I really am. But you can't be mad at me for that. It was totally out of my control and Nate and I have barely seen each other the past couple days."

Blair didn't classify movie night seeing them together as part of not seeing each other, "What about movie night?"

"I only talked to him for the first part of the movie and then went to see Dan didn't you see?"

Blair had to admit she left too early probably before this happened, "You mean you weren't with Nate the whole time?"

"No- ask Dan."

See? There is nothing to worry about, Blair thought to herself inwardly. She knew she tended to go a little overboard and act all controlling every once and awhile but she knew she needed to trust Serena on this.

"I'm sorry Serena I kind of over reacted. Given what has happened I kind of was nervous that it would happen again." Blair just knew in her heart that she needed to trust Nate if she wanted it to work between them. Just let go of all the insecurities.

"So have you been with Dan this whole time?" Blair asked.

"Yes. You see he got matched with this person called Nelly Yuki and he can't really stand her so-"

"He ditched her for you? Not surprising S," Blair interrupted, "I guess," Blair started putting her insecurities aside, "That I wouldn't have a problem with you spending time with Nate today at this carnival."

"Thanks?"

"You're welcome. You need something to write about for your paper."

"True or we could just make up the whole thing."

"Yeah well might as well not chance it. What if what you wrote differs completely from what Nate wrote?"

"That's true. Oh B, how's it been with Chuck?"

"Surprisingly not as bad as I had made it out to be."

"Really? No come-ons or anything."

"Well of course there are come-on's but its Chuck Bass. But he's my friend and I've actually had a good time with him."

"Thanks good to hear," Serena responded and suddenly her phone started ringing," Listen Dan's calling right now we'll talk later?"

"Defiantly."

Blair spun around to see Chuck re approaching.

"What did I miss?"

"Nothing that concerns you Bass," Blair replied.

Blair eyed the cotton candy cart and it was as if Chuck read her mind, "You want some cotton candy don't you?"

"You know me so well," Blair smiled.

As Chuck walked to the cotton candy cart Blair immediately had a pulsing thought of Nate. It has been like she'd forgotten about him. Blair instantly felt bad that she'd been spending so much time with Chuck and very little with her actual boyfriend. Blair instantaneously was reminded that she had a lunch date with him tomorrow and Blair was at ease.

Chuck handed her the pink frothy cotton candy. In that instant Blair realized she's been feeling happier and lighter the past two days then she has been in a while. She wasn't sure why but she didn't want it to end.

* * *

A/N: Review Please!


	6. Six

A/N: Thanks again for all the reviews! Just to let you know it might be a few days before the next update because lucky me, I'm getting my wisdom teeth out. So I decided to put out this chapter now rather than later. Hope you enjoy!

* * *

"You want your dad to invest in a strip joint how midtown," Blair commented as she scanned the dark atmosphere around her, while two stripers waltzed past her.

"A burlesque club," Chuck corrected, "a respectable place where people can be transported to another time. To feel free to let loose. No judgment, pure escape. What happens in Victrola stays in Victrola," Chuck finished giving his signature smirk at Blair.

"Well, it does have franchise potential. Chuck Bass, hard to believe all your underage booze and womanizing have finally paid off," Chuck scoffed.

"Truly I am proud," Chuck beamed at the compliment, "And you are my toughest critic-well second toughest."

Blair knew he meant Big Bart Bass. But then again who wasn't afraid of him?

"So, you think your father will go for it?"

"It is exactly the kind of innovative thinking upon which the Bass Empire has been built upon. It's perfect and I've been waiting for this."

Blair checked her watch, "I am so late."

"For what?"

"Lunch with Nate."

"Oh," Chuck said his lips forming a thin line and didn't say anything more.

"What oh?" Blair interrogated.

"How are things with Nathaniel lately?" Chuck instantly avoided her question.

"Just…Fine!" Blair replied and Chuck gave her a knowing look saying _you're lying. _

"Why do you ask?" Blair continued. She examined his facial expression and immediately concluded," You know something don't you? You'd tell me right Chuck. One of your closest best friends," Blair finished with an act of innocence.

"Oh no you don't. I'm not putting myself in the middle of this. I'm not telling you Waldorf."

Blair fuming at this response tried to think of a plan. She would never beg to Chuck so that was not an option-although Chuck would love to see her beg to him. Maybe the intimidation approach? No, Blair thought he was too much of her equal to cave.

"Fine. Are you coming?"

"Gotta pitch it to Bart."

Blair smirked and started to head for the exit. Chuck called after her, "Victory party here. Tomorrow."

"I wouldn't miss it," Blair replied as she walked out- she'd get that information just give it time.

"I'll send you a car," Chuck added.

"Don't be nervous, he's going to love it," Blair- even though she was mad- she still reassured him as she pushed open the door and entered the waiting limo. Chuck Bass the businessman who knew?

* * *

Later that day, Blair waited at her locker for her lunch date with Nate. Blair felt like she's barely seen him over that past couple of days and couldn't wait to finally see him.

Blair toyed with her phone impatiently. There had been no Gossip Girl blasts about Nate or Serena at all and Blair was relieved. Her firm request to Serena seemed to have worked so she didn't have anything to worry about. Well Blair was always worrying when it came to Nate. And the fact that Chuck had knew something was going on did not help her being paranoid.

Virtually every girl at Constance had a thing for him and most girls envied her to claim him as hers. Without being a powerful and demanding Queen B, Blair doubted that she'd even be with Nate. Her intimidation seemed to scare off most-if not all girls from even _thinking _about ever attempting to go after him.

Blair shoved her phone in her pocket and lifted her gaze to see Nate pacing towards her. The usual flutter that she would feel when she'd see him was not as poignant as it usually was. Blair shook the thought away.

"Hi sweetie," Blair greeted softly.

"Hey," Nate replied simply. He gave her a chaste kiss; it wasn't like those in the old Audrey Hepburn movies Blair adored but more like a Disney movie kind of kiss. At first she thought it was cute but…she wanted something more. Something that would make her stomach explode from the fluttering of butterflies taking flight. Blair shook that far off fantasy out of her head. Sometimes Blair's movie of her perfect life in her head wasn't always accurate.

"Ready to go?" Nate asked.

"Always."

Nate took her hand in his and walked out of the combined schools. All eyes were on the fairytale couple leaving, the usual whispers and gossip floating around them as they left. Nate and Blair had been dating for so long; she simply had tuned them out. They were just jealous.

They arrived at a French restaurant and were seated quickly. Nate didn't speak much during the taxi ride but Nate was more of the silent type. More physical to be exact.

"It's been so long, I felt like we haven't been together like this forever," Blair started smiling angelically.

"I know, with this Perfect Match stuff, things have really gotten in the way," Nate replied his eyes scanning the menu trying to decide what he wanted.

Or people getting in the way, Blair thought instantly. She attempted to make small talk, "How's lacrosse?"

"Good, we won our last game and moved up a spot in the league which we needed. You should have been there, I had this one play where…"

And just like that Blair tuned out. She didn't want to be rude but when Nate ranted on sports it would last for ages. And Blair never really cared about lacrosse. If anything she'd be happy to talk about tennis, field hockey but no of course the sport Nate would talk about incessantly would be the one she disliked the most.

A waiter appeared to take their orders cutting Nate off on his lacrosse play-by-play thankfully.

Nate ordered what he wanted and Blair simply picked a salad to eat.

"I didn't see you at the carnival yesterday. You were there right?"

"Of course," Blair said stating the obvious, "weren't you?"

"Yeah, "Nate replied, "Chuck's been good to you right?"

"It's Chuck of course he's good to me. He's your best friend of course he wouldn't do anything. I can take care of myself. Why are you worried?" Blair asked hopefully.

"No, I'm just making sure. You wouldn't be the first he'd try something with."

Blair hid her disappointment of Nate's lack of interest in her. The main entrees arrived and Blair pushed around her bits of lettuce and cherry tomatoes around on her plate. She barely made a dent in her salad when she put her fork down.

"How's Serena?" Blair finally asked the question she'd been dying to hear an answer for.

"You know she's Serena. Haven't seen her much, she spends a lot of her time with her boyfriend Dan." Nate replied while texting someone on his phone distractedly.

Blair simply nodded but didn't quite believe him. No matter how many times they can say they aren't attracted to each other, there is that possibility that they are lying. It wouldn't be the first time they both have to her.

"How are Howard and Anne?"

"Oh you know same old same old," Nate replied as he checked his phone and started texting again.

Blair still wanting to know what was going on knew there was nothing else she could ask him. Blair kept her mask despite what she was feeling.

Blair then felt the urge to gorge. Her stomach rumbled loudly and Blair scarfed down her salad and at least four slices of baguette.

Nate paid the bill and they hurried back to school trying to make it in time before class started. They arrived back where Nate kissed her goodbye. Still no fireworks, Blair noted.

Blair made a beeline for the bathrooms. She knew what she had to do. It was her escape. She made sure nobody was in the girl's bathroom and made sure to lock the door behind her.

Blair opened a bathroom stall door, crouched down and purged.

* * *

Blair finished and wiped away any sign of what she did trying to make it as though nothing had happened. Finally pleased and relieved of getting that feeling out of her system she unlocked the bathroom door and almost physically ran into Chuck.

"Sorry Waldorf," Chuck apologized, "You should be watching where you're going." Chuck looked at her noticing by her pale cheeks and looking through her mask she had been wearing for so long and asked, "Waldorf what's going on?"

* * *

A/N: There will be more of season 1 scenes integrated in the upcoming chapters and I had to include Blair's bulimia. Anways please make my day and review!


	7. Seven

A/N: Thanks for all the reviews and support guys! So far the pain hasn't been too bad so I hope it stays that way! Anyway, enjoy!

* * *

Wow wait, Blair thought inwardly to herself, since when did Chuck Bass EVER care about anyone but himself?

"Seriously Waldorf are you okay?" Chuck pressed showing some concern for her. He could read her like a book, and knew her well enough to see through her charade.

"Of course I'm fine," Blair snapped, "Is this your new way to pick up girls? To be nice to them now?" Blair asked diverting the attention from herself and not even looking at Chuck as she tried to walk away from him. Well, more like run.

"I would but that's just not my style. Once a devil, always the devil- hey Waldorf slowdown will you!" Chuck said trying to keep up with her.

Blair didn't answer and Chuck asked,"Are you still mad at me from this morning?"

Blair didn't answer but kept walking faster.

"Blair, Blair!" Chuck said trying to get her attention but Blair kept ignoring him.

"Alright fine I'll tell you."

Blair stopped dead in her tracks and whipped her body around to face Chuck.

"But you didn't hear this from me got it? If you tell him I told you I will deny this and thus get back at you for it are we clear?"

Blair nodded. These were always the terms when one or the other had to tell some secret to the other.

Blair had it settled in her mind that the secret had to be that Nate still loved Serena and they want to be their own couple, kicking Blair out to the curb. That had to be it, it was the only explanation it-

"The reason Nate wanted to be your girlfriend again was not because he liked you. It was because he needed to use you."

Wait what? Blair screamed inside herself.

"His father is losing money and to make the deal with your mother he needed Nate to date you so he could close the deal with your mom."

A couple seconds passed before Blair found her voice to speak," That's impossible, Nate loves me."

"I'm just telling you what he told me. Especially after the masquerade ball he hasn't been the same. You wanted to know Blair."

Blair resisted the urge to walk right back into the bathroom and purge all of her feeling out into one of the toilets. This changed everything. Nate didn't even make an effort to find her at the masquerade, this would explain why. He didn't want to be with her simple as that. She asked to know the truth and now she did. The problem remained as to what she would do with it. Blair spun around and walked away and ignored Chuck calling after her.

* * *

Later that night was the dinner Eleanor had planned with the Archibald's. Blair sat in her bedroom wearing what looked to be what old women might wear. She wore a baby turquoise lacy dress with black Michael Kors high heels. She fastened one of her signature black headbands against her wild chestnut curls and applied a bright ruby red shade of lipstick. Blair knew she looked great on the outside but didn't feel the same in the inside.

Even after Chuck told her Nate's true agenda, even little Jenny Humphrey had come to tell her even more bad news. Blair recalled what Jenny had told her.

"_At school two weeks ago, when you saw me with Nate he wasn't talking to me about what to give you. He-" Jenny paused tears ready to escape her eyelids as she took a shaky breath, "was apologizing for what happened at the masked ball."_

"_What happened at the masked ball Jenny," Blair demanded starting to shake with rage knowing what was coming._

"_He told me he wasn't over Serena," Jenny replied quietly, _

"_Why would he tell you that?"_

"_Because I was wearing her mask and he thought I was her," Jenny looked like she was ready to start crying, "He kissed me"_

"_That's enough Jenny," Blair replied calmly and viciously. Yes it wasn't really little Jenny Humphrey's fault but Blair couldn't help but blame her._

"_Blair I-I didn't want you to find out-"_

"_You're dismissed Jenny. For good," Blair commanded._

"Blair, our guests are here!" Eleanor called from the foyer of their penthouse. Blair wiped away the tear that had fallen down her soft cheek and reluctantly made her way downstairs to meet the guests.

"Hey," Nate kissed her cheek, "You look beautiful tonight."

Blair fake smiled at him. He had a lot of nerve. Blair suppressed her anger she had for him and just greeted Anne and Howard as if nothing were wrong. That everything was actually normal and her mask never ceasing to crack.

A flutter of conversation had aroused about Howard and Eleanor's almost business deal. Now that Blair knew their true motives Blair realized how oblivious she was before. It was painfully obvious and she didn't have a clue.

"Enough business talk Howard, your boring her," Anne interjected her husband's rant.

"Now I was thinking when Nate and Blair get engaged she could have this ring, it's my great grandmothers," Anne showed it off proudly. Blair was still stuck on the fact that it was _decided _that she and Nate were assumed to get engaged. He clearly didn't love her-which apparently Anne was unaware of.

"It's beautiful," Eleanor commented in awe.

"Blair why don't you try it on?" Anne asked.

"Oh no I couldn't-"

"Oh please but you must," Anne pressured, handing her the ring.

"Mom she said she doesn't want to try it on," Nate interjected.

"Nate please," Anne hissed and glared at her only son.

Blair slid the massive rock on her finger, "It fits," She noted actually smiling. It did look nice and all on her.

"How about for a toast everyone? Bottoms up!" Howard spoke. Blair always noticed he spoke two times faster than any normal human does. Maybe it was just her that thought so though.

"Hey dad why don't we go smoke those cigars we got?" Nate questioned noticing his father's empty wine glass sitting on the glass coffee table.

"Sure thing son!" Howard said. The two Archibald men exited the room when it got unusually quiet.

"I just have to go get something from my room," Blair said quickly avoiding the awkward silence that would ensue.

Blair made her way to the window of her bedroom and looked down. She saw the scene before her between Nate and his father. She saw with shock as he punched out his dad and how he paid the doorman not to say anything.

Blair stormed down the stairs and to the elevator. She needed to know what the hell was going on.

As soon as the doors parted on the ground floor Blair sauntered to Nate whose back was facing her. He was opening the door to the limo pulled up to the curb when Blair interrupted him and slammed the door shut, "What are you doing?"

"I'm going to Victrola, I promised Chuck, it's important to him."

"I saw your father get arrested. Why didn't you come to me? I would have listened!"

"I tried Blair! But every time something's got your attention. A dinner party, the masked ball, this perfect match thing-"

"Yeah let's talk about that masked ball, let's talk about how when I was waiting for you to find me so we could finally be together you were confessing your feeling and kissing Serena!" Blair's voice started to tremble and she could feel tears coming to her eyes as the memories flashed before her.

Blair continued, "I thought I was doing everything right-"

"It's not your fault," Nate mumbled.

"Do you love me?"

Nate did not answer and Blair put her head in her hands and shook her head, "you should deal with your father he needs you, "Blair swallowed the lump that had formed in her throat, "you know what? I don't," Blair turned and got into the waiting limo which sped away. Strangely she didn't feel any hurt or sadness as the limo moved further and further away. She meant what she said. It was over.

* * *

"Where's Nate?" Chuck asked when Blair arrived at Victrola not twenty minutes later.

"I think we just broke up," Blair stated.

"Wait what?" Chuck asked not believing what he was hearing.

"I don't want to talk about it. I just want to escape. That's what this place is for right?"

Chuck smirked at her and led the way into the bustling nightclub.

They approached a large suede couch that sat in the middle of the room filled with many other tables. Many people were cheering and hollering at the burlesque dancers and Blair watched never having seen this type of dancing live before.

"Look, I know you don't want to talk about it but-"

"Relief. I feel relief," Blair didn't break eye contact with the dancers on stage, "You know I got moves."

"Come on your ten times hotter than any of those girls on stage."

"Stop it Bass. I'm just saying I've got moves," She looked at Chuck who clearly didn't believe her.

"You really don't think I'd go up there?"

"Oh I know you won't go up there," Chuck challenged her.

"Guard my drink," Blair said silently accepting the challenge and made her way to the stage and for once acted totally unlike Blair Waldorf. She felt free and careless and enjoyed every minute. It also helped that no one including Chuck could keep their eyes off her. The attention was on her for once and she finally shinned.

* * *

Chuck led her to his waiting limo opened the door for her and Blair felt herself collapse inside. She couldn't believe what she just did or that she was only wearing a white slip dress right now. If she rewinded to twenty four hours ago and was told she was about to do this she probably would have fainted.

Chuck got into the other side of the car and he told Arthur to go to the Waldorf penthouse.

Blair felt herself ease back into the utterly comfortable leather seat. A comfortable silence overtook them both.

"You were amazing up there," Chuck said in awe as he looked at her.

Blair didn't know if it was the champagne of what but she felt herself move closer to Chuck. Her body clearly wasn't listening to her brain as she continued to get close to him and finally kissed him.

Wow. That was all Blair could think of when Chuck's lips were on hers. Those petty sparks that would fly with Nathaniel paled in comparison as to what she was feeling with Chuck. She was feeling the fireworks and neither pulled away for what felt like eternity but only lasted a couple seconds.

Chuck pulled away and Blair looked at him confused.

"No- Not like this. You're not like other girls. I know you want it to be special."

"What are you talking about? This is special enough," Blair said. Okay, maybe the alcohol was talking just a little bit, but she was sick of having her perfect plans ruined. Sometimes things aren't going to go your way and Blair knew she has found this out the hard way.

"Trust me, you would regret this and deserve better."

Blair noticed the car come to a stop and turned her back on Chuck. She opened the door and stumbled out only hearing Chuck call out to her, "Blair I'm sorry!"

Blair ignored him and made her way up to her bedroom and collapsed backwards on her bed. Drowsiness suddenly overcame her where she was taken to a dreamless sleep wishing tonight never happened.

* * *

A/N: *Ducks under desk* Don't kill me! I had to throw a curve ball in there! Call me evil but I didn't want this to be too predictable, it'd be too boring! Anways let me know what you think and **review**! :)

Also thanks to one of my wonderful reviewers Alicia Cybula check out this new Chuck & Blair video on youtube (Its also on my profile if you can't access it)

h t t p : / w w w . y o u t u b e . c o m / w a t c h ? v = N u 9 6 M D r T 8 E w (remove the spaces of course)


	8. Eight

A/N: Thanks again for all the reviews and support guys! I appreciate it! So this chapter is quite significantly longer than all the others and alot happens in this one so I hope you enjoy and please review!

* * *

Blair awakened the following morning to feel a cold draft chilling all the bones in her body. Blair slowly opened her eyes to see her laying on her bed without any covers on or change of clothes. Blair confused as to why this was sat up and made her way to her en suite bathroom. She looked at her retched reflection in the mirror when the events of last night flooded through her mind.

"_No- Not like this. You're not like other girls. I know you want it to be special."_

Oh my god, Blair thought, I almost gave my virginity to that-that Chuck Basstard!

This week had been all too weird for Blair and the fact that Chuck refused her… why would he do it? Blair thought as she stood up.

He told me he liked me, Nate and I broke up, I made a move and he did nothing. The _normal _Chuck Bass would have taken this to his advantage and swiped her v-card.

"_Trust me, you'll regret it." _

Chuck's voice rang in her head reminding her of this. Of course I would, Blair thought for once Chuck Bass took someone else's wants instead of his only. What will happen next the world actually ending in 2012?

Blair brushed her teeth and washed her face; the usual routine she would do in the morning before leaving for school. Blair then applied a generous application of eye shadow, eyeliner, and mascara. She then applied her ruby red lipstick feeling more Audrey like then ever.

She was now free on the market. Well, no one knew yet but… Blair realized maybe they won't have to know. Nate and I will probably get back together shortly anyway, Blair reasoned. And Chuck was only a little blip.

Until she remembered the kiss. Maybe he was a hill not a blip but that kiss meant _nothing_.Nada. Zip.

Of course there wasn't any _fireworks _with Nate, but-but. Blair stopped her thought process there and decided to live in oblivion and to also ignore Chuck Bass all together.

Blair pulled on her uniform added her ruby red heart ring and signature headband collected her books in her bag and headed out.

Dorota was waiting with a silver tray of berry yogurt, apple slices and a croissant in the living room.

"Good morning Miss Blair, did you have good night?"

"It was fine," Blair replied as if no inner dilemma were occurring in her head at the moment about what to do with her current situation, "Now I'll just go, I'll be late for school," Blair concluded turning around towards the elevator in the apartment.

"But Miss Blair you ought to have good breakfast!" Dorota protested. Blair whipped around took a couple strides towards Dorota. She took two apple slices and proceeded to leave.

"Thank you Dorota. Have a nice day," Blair added politely.

As soon as Blair emerged onto the crowded New York street the sun blinded her eyes and a fierce wind hit her from her right side. Immediately not wanting the wind to ruin her hair, Blair hailed a cab and told the driver the directions.

Blair felt her phone vibrate in her bag. She opened it up to see a new Gossip Girl Blast. Great just what she needed.

_**Looks like another good girl has gone bad. Step aside Lindsay Lohan, because Queen B is now making her mark on the dark side.**_

_**Xoxo Gossip Girl**_

What? Blair looked astonishingly at the photograph in front of her. It was a picture of her dancing at Victrola last night.

That basstard.

Great this is just what I need, my reputation to go down the toilet, Blair thought miserably. Blair sat back thinking of ways she could torture Chuck Bass. And she came up with nick names like Chuckles (he would HATE that one), Mother Chucker (Ha!) and Chuck Basstard.

Blair's phone vibrated again, disturbing her from her revenge plots from a text.

_**Hey B!**_

_**Haven't heard from u in a while! Ready for the ball tonight? I say we get ready together and catch up! Let me know school!**_

_**Xoxo S**_

Shit. Blair had totally forgotten about the ball. The ball that she planned to lose her virginity with Nate to. That one.

Blair had the urge to send a text back saying, sorry I'm not coming, but restrained. Being the Queen B of Constance meant you always had to show up to all social events. Unfortunately when you don't want to see specific people that makes this commitment a pain in the ass.

The taxi came to a slow stop and pulled over to the side of the road. Blair paid the amount and stepped out of the car slamming the door behind her.

She entered the gates of the school to have people looking at her like they always did and whispering about her. This time though, she knew what it was about.

Blair kept her head held high and made her way to her locker. She twisted the combination on the lock and snapped it open, releasing the wooden door and unveiling the contents of her locker.

"Waldorf," a voice said behind her. Blair felt the hairs on her neck stand up realizing who the voice belonged to. The last person she wanted to see.

Blair whipped around to face Chuck Bass face to face. He was smirking in all his Bass glory, and Blair narrowed her eyes, "What do you want?"

"Just to say good morning to you Blair and about last night-"

"Oh don't even. Why would you think it was okay to send pictures of me dancing at Victrola from last night?"

"Wait what are you talking about?" Chuck asked confused.

"Let me see your phone," Blair demanded hand stretched out facing up.

"Okay," Chuck said clearly not understanding, "I would never send any pictures to anyone let alone Gossip Girl of you Blair."

Blair looked at him in disbelief. He is Chuck Bass after all. Social destruction was his specialty.

"You don't believe me do you?" Chuck said handing his phone over.

Blair looked at the messages to see an unopened one from Gossip Girl. Crap. He _was _telling the truth.

Blair opened the message and showed it to Chuck.

"Oh, well you danced beautifully last night."

"Yeah stripping down to nothing but a slip dress! This is terrible don't you see Chuck?"

"Waldorf you need to not take everything so seriously. If anything everyone will admire you or be even more in awe of you to know you have a wild side. Intrigued even."

Blair gaze met his and he could tell she wasn't convinced.

"If anyone asks just say it was a dare or something which it kind of was anyway."

Blair turned back towards her locker grabbing her AP chemistry textbook and binder and AP English binder.

"Look I'm sorry for how last night ended. And to be fair, you kissed me and I stopped you from well..."

"Well don't expect anything like that to ever happen again. As a matter of fact, I think we should spend some time apart."

"Well I'm supposed to escort you to the ball and since you are now Nathaniel-free- I feel much less guilty about taking you."

"You will not be taking me anywhere!" Blair hissed. She slammed her locker closed and met Chuck's gaze. "Got it?"

"Yeah sure Waldorf," Blair's shoulders relaxed, "I'll be picking you up at seven." Chuck strode away giving her no opportunity to protest. That mother Chucking Basstard.

* * *

Taking up Serena's offer, she and Serena got ready at the Waldorf penthouse for the ball. Serena came a little after four giving ample time to get ready and leave before that Motherchucker arrived.

Both girls were in Blair's bedroom and even though she wouldn't admit it out loud, Blair was glad Serena here. Her absence was not forgotten and Blair needed her best friend.

"So was that really you in that picture on Gossip Girl this morning? You can't see the persons face in the photo," Serena asked slipping on a green cocktail dress.

Blair examined it shook her head signifying that it was a definite no to the dress.

Besides the point, Blair knew she had two options. She could one lie to Serena and say the photo was of some look-a-like from behind skank, or option two come clean to the embarrassing events of last night and her breakup with Nate.

Option one was looking better that the moment.

"No, it's probably just some skank from Chaplin. Let her enjoy her five seconds of Gossip Girl fame," Blair answered with ease. See lying was always her forte.

"That's what I thought B; I never would believe you'd do that anyway."

Have I really become that predictable? Blair thought instantly. Sure she always had a schedule-more like routine- but she was capable of letting loose and having some fun. Was that so hard to believe?

"How's Cabbage Patch?" Blair ask using the nickname she'd come up with when Jenny told her Dan had a cabbage patch named Cedric.

"He's good," Serena replied while trying to decide which of the two dresses she was holding to try on. She tossed the silky red dress on Blair's bed.

"How are things with Nate? I saw that thing about him in the paper today," Serena asked as she zipped up her chosen dress. It was more of a peachy dress which accentuated her cleavage and bubbled out from her narrow waist. It was a perfect spring dress.

Blair was again forced to make another hard decision. Lie or tell the truth. Blair knowing that Serena was matched with Nate for Perfect Match knew that she'd find out eventually. Shouldn't she have already?

"Nate's been going through a tough time right now. Did you see him last night at all?" Blair replied smoothly turning the conversation away from her.

"No actually, we haven't spent that much time at all together this week. I was with Dan last night."

So Serena didn't know, Blair concluded. If she did she would have brought something up by now knowing Serena and all.

Blair decided on a black dress. She was in fact, in a time of mourning without her boyfriend. She paired it with black stockings and bright red Loubouton heels.

She was a free woman now, what better time to make a fashion statement?

Serena and Blair continued to ready themselves and after six, Serena got a text from Dan.

"Oh B, I'm sorry but I have to go. Dan just texted me wondering where I was and he's waiting at the penthouse," Serena rambled, "Are you okay if I leave? Can I go?"

"Of course!" Blair responded faking her enthusiasm. Serena smiled brightly and Blair knew she bought it.

Serena gave her a hug, "I'll text Nate to come get you. If anything you should be escorted by your boyfriend."

"Don't worry about it. I will myself! I- I had something special planned for him anyways," Blair covered. Well it was partially true. It was supposed to be Valentine's Day after all and she had planned to become a woman tonight.

"You don't mean?" Serena asked in disbelief.

"It's not any of your business Serena. These things are private," Blair pushed her towards the elevator," Now go meet Humpty Dumpty before he thinks you went with someone else."

"Okay," Serena stepped inside the elevator pushed the button to go to the ground level and turned around," B? Just don't do anything you're not ready for." The doors glided shut smoothly and Blair thought to herself, don't worry S, there won't be any decision tonight anyway.

Blair climbed back upstairs to gather her things. She gathered her cell phone, lip gloss, and other essentials to go in her black clutch, grabbed her longer evening coat and was ready to leave when she heard Dorota call from downstairs, "Miss Blair, Mr. Chuck for you!"

What? Blair furiously exclaimed in her head. Of course he kept true to his word. I told him NOT to come here or talk to me again! Blair fumed but held a cool exterior.

Blair descended down the stairs stomping angrily to be greeted with the smirking, nauseating and annoying Chuck Bass.

"What are YOU doing here?" Blair exploded angrily. She figured if she left earlier than seven then she could avoid Chuck until the ball. But he showed up _early._

"I told you I'd pick you up at seven and came just a little ahead of schedule. You look ravishing Waldorf," Chuck's eyes gave a once over and Blair couldn't help but feel heat come to her cheeks. It felt like he was looking at her naked or something. It was weird.

"Are you ready to go?"

"Not with you," Blair retorted sharply. Seriously did Chuck ever get the message? Blair fumed.

"Lots of people would be honored to be escorted by Chuck Bass as should you so yes you are kind of obligated to go with me. You are my match after all."

"Only on paper-"Blair argued.

"You know it's funny because I don't think that their survey was too far off. We both love to destruct others and humiliate them, we do share superior wit amongst the rest of our classmates-"

"That's the only thing we will EVER have in common Chuck!" Blair snapped. I would never want to be like you almost rolled off her tongue but Blair stopped it.

"Look, the only reason I stopped you last night was because of Nate," Chuck said changing the subject.

"You didn't want to ruin your friendship? That's so sweet," Blair replied sarcastically.

"It was about time you realized he wasn't meant for you. Waldorf you need someone that is your equal. Nate was just a pretty face, and nothing more to back it up."

"That's preposterous. Nate loves me; we're just going through a rough patch is all."

Chuck rolled his eyes," Please when are you going to get it? Face it; you ended it yourself last night. It's over."

"Why do you care so much?" Blair asked. Chuck looked away thus not answering Blair's question.

There must be a reason for this nonsense, something that he always treats me differently from any other girl, is happy that I broke up with Nate it could only mean one thing, the wheels were turning in Blair's head.

"Do you… like me?"

Chuck didn't immediately answer," Define like."

"Oh no, no, no, no. This cannot be happening!"

"How do you think I feel? I haven't slept, I feel something in my stomach…fluttering," Chuck exclaimed.

"Butterflies?" Blair said. She was beginning to feel the room spin with this revelation.

"Trust me no one is more surprised or ashamed more than I am," Chuck looked disgusted with himself.

"Chuck, you know that I adore all of god's creatures and metaphors they inspire, but those butterflies," Blair swallowed," have got to be murdered."

Chuck looked hurt, but quickly covered it up with anger, "Fine. It wasn't that great anyway."

"Good. Now if you'll excuse me I will need to be going-"Blair said trying to avoid the awkward silence, "Or how about you actually do what I say and go."

"Fine, I'll see you there Match."

Blair was about to say the last word untill the elevator doors shut. Blair waited a few minutes and checked her makeup before finally making her way down the elevator and into the waiting car. This gave Blair some time to ponder.

She was really flattered that Chuck liked her of course she was. It just… would never work. He probably would want to use her once then that would be it. And they couldn't be friends anymore. Chuck was one of Blair's closest friends and she didn't want to lose him.

She arrived at the ball and it was almost a half past seven. Twenty minutes was always the best time to be fashionably late.

Just as Blair stepped out of her car she saw Chuck get out of his limo. Great timing Blair thought grimly. Chuck didn't do so much as look at her and proceeded into the building.

Blair sighed to herself, honestly that man can be more dramatic than I can! Blair thought as she rushed to catch up with him.

"Are we really going to be like this now?" Blair asked almost to the point of exasperation. She just wanted everything to go back to normal- before this week ever happened. All Blair wanted was for them to go back to being just friends.

"Like what?"

"Just being careful around each other. Chuck come on, your one of my closest friends. Can we call a truce?"Blair held her hand out in anticipation.

"For you Waldorf, of course," Chuck shook her hand and Blair felt a shot of electricity shoot through her at his touch.

Blair hastily let go before any gossip girl pictures could be taken.

"Come on Waldorf," Chuck offered his arm for her. Blair felt herself relax and took it. See? Blair thought now I just need to hatch a plan to get Nate back and everything will go back to normal.

Chuck led the way and into the ballroom. Blair looked around to see that it was dimly lighted, had a sprawling dance floor which took up most of the room and was practically filled at this point with high school kids. There were massive chandeliers that hung from the ceiling and some tall tables lined with white linens that were evenly spread out around the exterior of the room.

"I'm going to go look for Serena," Blair told Chuck before disappearing into the crowed room.

In truth the thing Blair was feeling most was confusion. She knows she shouldn't like Chuck, but maybe there was something? And he does treat her differently than all the other girls in their grade. Is that a coincidence? Blair didn't think so.

Blair knew that what she felt when she was with Chuck was more then what she could ever feel with Nate deep down, but she would never admit that to anyone. It had been a struggle to admit it to herself.

If she were to admit it to anyone it would be Serena. Maybe it would be best to come clean.

Blair's eyes then scanned the dance floor in search for Serena.

"This is pointless," Blair mumbled to herself. Blair texted where are u? to Serena.

Within two minutes Serena responded.

_**On the dance floor with Dan. I finally got him to dance! Come join!**_

_**-S**_

Well that was helpful, Blair thought sarcastically as she looked onward towards the clump of people littered on the dance floor.

"Where's your other half Queen B?" Blair turned around to be faced with her minions. Just the people she wanted to see. Not.

"Well not that it's any of your business girls but he is here. He's just not glued to my side all the time. If you'll excuse me I'm looking for Serena," Blair pushed past her minions and circled the perimeter of the dance floor. You'd think a tall blonde girl would be easy to spot.

The music started to slow into a slower song. Couples swirled on the dance floor and finally Blair spotted her with Nate. Of course.

"Waldorf care for a dance," Chuck appeared beside her offering his hand out to her. Blair looked from Nate and Serena to her minions snickering off to the side and back to Chuck. She put her hand in his and again felt a surge of electricity pulse through her. Why does this keep happening? Blair thought.

Chuck lead her further onto the dance floor and draped his hands comfortably around her narrow waist.

It hasn't even been a day and he was already all over Serena? Dan was so going to hear about this. Blair held her eyes fixated past Chuck. Nate's eyes creased and he threw his head back into a fit of laughter. He was laughing and joking. He seemed happy. She could only see the back of Serena's head but could imagine her four year old sounding laugh escaping from her lips.

"Is something wrong Waldorf?" Blair snapped her attention back to Chuck his eyes holding a serious look on her. He looked back and saw Nate with her. "Ah."

"How could he? It's only been a day!" Blair blurted.

"Well to be honest Waldorf, you barely waited an hour," Chuck smirked back at her.

"But I never cheated on him! He's always loved her. I thought that I could make him love me but he never will. First the Shepard wedding, and the masquerade ball…"

They both swayed to the music in silence. Blair figured Chuck wouldn't know what to say.

"It's his loss," Chuck finally responded.

Blair rolled her eyes," Yet he'll never know that until I'm gone isn't that the old saying?"

"I'm the last to ask but that sounds familiar."

"Chuck…" Blair paused finally asking a question she wanted to ask all week, "Why are you being so nice to me? It's just so not you?"

"psh, I'm not being nice, I'm just being there for one of my best friends. Just like when she was when I needed it before."

Blair smiled, but didn't comment any further. They held the gaze as if they held a secret no one knew about.

The song ended and the music was replaced with another upbeat fast song.

"I'm going to go talk to Serena, I'll be right back."

Blair heard the sound of phones beeping around and everyone staring and pointing at her.

Blair walked briskly away and finally found Serena her arms linked to Dan's.

"Oh B you missed it! I actually got Dan to dance! Can you believe it?"

"If you count pumping my fist into the air and jumping up and down then yes I did dance."

"That's nice Humphrey," Blair replied coolly, "Serena can I talk to you for a minute?"

"Uh sure."

Both girls walked aside and sat at one of the vacant tables.

"Have you seen Nate tonight?"

"Uh no I've been with Dan all night. I thought you said he was picking you up?" Serena asked confused.

Logically it wouldn't make any sense for Serena to have been dancing with Nate at the time she was with Dan. Blair sighed and with all the evidence she was forced to believe her.

Blair knew it was time to tell the truth, "Well you see the thing is-"

"Blair I can't believe he did this to you!" Hazel exclaimed. Penelope and Iz remained at her heels.

"I hope he gets herpes!" Penelope chimed in.

"Definitely, cheaters deserve herpes!" Iz added.

Oh no.

"What are you guys talking about?" Serena asked even more confused.

"Nate was caught cheating with another girl, here tonight. He was dancing with another girl and showed some affection for her. There are pictures on Gossip Girl."

Can't the madness stop! Blair's mind raced frantically.

"What? B," Serena placed her hand over Blair's, "I'm so sorry."

That did it for Blair," There's nothing to be sorry about," Blair took a deep breath, "We broke up okay?"

Serena just stood there in disbelief, "I didn't want anyone to know because the more I denied the better chances we had to get back together!" Blair felt her eyes watering when Serena extended her arms and wrapped them around her.

Blair let go breathing in another deep breath, "Excuse me, I just want to be alone."

Blair got up and quickly fled the ballroom.

_**When Cinderella fled from her ball she left a slipper, as for our queen B she left a king. A cheater revealed on Valentine's day? Harsh. We're all here for you Queen B.**_

_**-xoxo Gossip Girl**_

Blair grabbed her coat from coat check and exited the building. The cold air smacked her in the face as she exited. Blair started walking; they say that's what you should do when you wanted to think.

Blair on the verge of tears passed a group of people when she felt a hand grab her elbow and called, "Blair!"

Blair spun around to see Chuck standing there grasping her arm.

"Where are you going?"

"Away from there obviously. I'm going home."

"You're walking? That'll take an hour. What happened?"

"So what, I need time to think," Blair answered avoiding his other question.

"Waldorf, come on why don't I give you a ride home."

"No thanks I want to be alone."

"But Waldorf, if you intend on walking you're going in the wrong direction."

"I'll find my way."

"Waldorf come on, no talking just a safe ride home."

"Aren't you staying though?"

"No- I found it was getting a little dull in there."

"What are you talking about? Everyone just got the news of the decade! The Queen and King have broken up!"

"I've head stuff that was way more scandalous. Come on Waldorf."

Blair stood there and regretting followed him into his limo. All Blair knew was that she needed to get out of there. Get out of the battlefield and into the safe zone.

A few minutes of silence went by when Chuck said," I know you don't want to talk but I just have something I want to give you."

Chuck pulled out a large, square velvet box.

"What is that a sex tape?"

Chuck smirked and opened the box.

Bliar felt her eyes widen, "It's the Erickson Beaman necklace," it was the necklace she asked for, for her birthday in November. The one she wanted the most and no one got it for her, "You can't…won't…" Blair stuttered. Chuck smoothly took out the necklace and fastened it around her neck. He smoothed out each pendent and Blair saw her reflection through the window.

"Something this beautiful should be seen on somebody worthy of its beauty."

Blair's mind was completely turned off. This is completely absurd. What? How? Why? So many questions with so few answers.

"I really am sorry. For what's happened this past week, I hope this could somehow make up with it. Happy Valentine's day Blair."

Blair turned her head to face Chuck head on. They were only inches apart and Blair could feel the magnetic pull towards him. She moved closer and sealed a kiss conveying her forgiveness. She couldn't resist any longer.

No words were needed to express what they both were feeling in that moment. For once Blair realized that actions do speak louder than words.

They broke apart and Blair could feel the fireworks, along with a churning stomach. Blair knew what was going to happen. And she wasn't going to stop it. It was time.

Blair leaned back in and so did Chuck and they kissed once more. Chuck wrapped his arms around her and pulled her on top of him.

Blair started to lose herself feeling things she'd never felt before when they felt the limo come to a halt.

Chuck surfaced for air and was about to tell Arthur to take them around for a few more blocks when Blair stopped him.

"Come in," She knew Chuck meant into the Penthouse and in her room.

A few minutes later they stumbled into her room, kissing and removing clothing. Blair slipped off Chuck's jacket and pushed him backward on her bed. She didn't really know what she was doing but felt comfortable with Chuck there.

Chuck only looked up at her in awe as Blair removed her carefully constructed bun and let her curls bounce to their normal positions.

Blair bent down to kiss Chuck again and let him take over. Sure she had all the words from Nate, but it was all talk. But with Chuck there were more actions and that spoke louder than any of the words Nate could ever say.

* * *

A/N: And Chair is FINALLY together for the first time! Hope you guys enjoyed the chapter! Please Review and tell me your thoughts!


	9. Nine

A/N: Thanks for all the reviews! You guys really are amazing!

Disclaimer: I do not own Gossip Girl or any of its characters

* * *

Sunshine peaked through the curtains as Blair woke up the next morning. Thankfully it was Saturday, and she was able to sleep in. It was almost eleven thirty. Blair turned to the other side so the sun didn't face her. She opened her eyes lazily to see Chuck beside her sleeping peacefully. He had his arm draped protectively around her, his lips parted slightly.

Blair snuggled a little closer to his form, when reality suddenly hit her. She lost her virginity to Chuck Bass. Blair bolted upright pulling the covers higher trying to conceal her nude form. Had Dorota seen her? Or worse, her mother?

Blair looked back horrified to see Chuck completely naked, yet still asleep. Blair pulled the covers up to see… she was only curious and was a little more preoccupied last night with his amazing… well never mind.

He had a nice package, Blair will admit. So she was never really exposed to any other male's private parts but from the talk of all the other girls who've been with Chuck they've all said he wasn't small. Apparently that was a good thing.

Blair noticed her room littered with all their clothes scattered on her bedroom floor. She noticed her underwear all the way near the doorway. How did THAT get there? Blair thought alarmed.

Blair turned to Chuck and slapped him with quite a bit of force on the arm to wake him.

"Ow!" Chuck moaned sleepily as he opened his eyes squinting letting his eyes readjust to the light.

"What the hell was that for?"

"You have overstayed your welcome Bass. Get up!" Blair slapped him again, in the same spot and even harder.

"What the fuck Waldorf! For once in your life can you stop being so abusive? You were much more cooperative last night."

Blair made another attempt to swing for another slap but Chuck caught her wrist and pulled her close to him, "calm down Waldorf. It's probably not even noon yet so relax."

He brushed his fingers down her back and Blair responded feeling goose bumps rise on her whole body.

"Chuck about last night-"

"If you're about to say that it never happened let me remind you that it did, I warned you about this and that you were completely sober when it happened."

Well, he did have a point-not that she'd ever admit to that.

Then, Chuck stated kissing from her elbow up to her shoulder and then proceeded to the nape of her neck.

"Miss Blair," Dorota was knocking on the door.

Blair threw off the covers pushed Chuck off of her and hastily ran to the door, holding it closed. Now would be a beautiful time to have a lock on it.

"Yes Dorota?"

Dorota tried to open the door but Blair used all of her ninety five pounds worth of weight to close the door. Dorota gave up and replied, "Miss Serena here to see you."

"I'll be there in a minute go tell her that, I'm just…" Blair looked to see Chuck enjoying the view he had of her laughing silently, "getting changed. I won't be long."

Even though Dorota has helped her get dressed and has walked in while she was without Blair having any problem, Dorota seemed to buy it. She heard her maid click down the stairs and backed away from the door.

Blair scrambled retrieving her clothes and throwing Chuck's clothes at him. She tossed all of hers in her laundry hamper and turned to Chuck who was eyeing her hungrily.

"Enjoying the view?"

"Oh yes I am. The best I've ever seen. "Blair felt herself blush but continued to put on a fresh pair of underwear and bra with then topped it with a silk nightgown and robe. She quickly examined making sure she didn't scream I-just-lost-my-virginity-to-Chuck-Bass.

Blair then made her way to Chuck and told him," whatever you do stay here and DON'T move!"

"I thought I overstayed my welcome?"

"Just do it Bass," Blair replied exasperated and then threw the covers over his head.

She hurried down the stairs to see Serena waiting for her.

"You slept in quite late," Serena said. She clearly must have been waiting a while.

"Yeah I was really exhausted."

"I just wanted to see how you were doing B. With last night and all. Are you okay?"

"Yeah, I just should have been honest about it from the beginning. I just didn't want it to show up on Gossip Girl you know?"

"Yeah I do, I just never thought it would happen. You guys have been together forever!"

"Well Serena, you must of known we had it coming," Blair replied coldly. She after all was one of the reasons why she and Nate broke up.

"But anyway," Blair said, "It was time. I mean, it just wasn't meant to be."

"That's very mature of you B, you're taking it a lot better than I thought because of last night in all."

"Well I got the truth off my chest and let out how I was feeling I guess," Blair said.

Serena's phone beeped and she checked her message," Oh its Dan, he has a surprise for me. Look B, I have to go but if you ever need help or someone to listen I'm always here. And we need to have another sleepover soon!"

Blair laughed if only she knew Chuck and her well did that on her bed she would never sit on that bed ever again, "Agreed. Thanks S for dropping by," Blair said genuinely.

"I'm back for good now B, if you need me I'll always be a call away," Serena pressed the elevator door button and the doors parted.

"Good," Blair smiled.

"Oh B, where did you get that necklace? I've never seen it before?"

Blair looked down to see the necklace Chuck gave her, "Oh it was a gift from a really great friend."

"It's beautiful B," Serena stepped into the elevator.

"Thanks S," Blair beamed.

The doors glided shut and Blair walked down the hall left of the elevators to the table and mirror. She looked at her reflection to the necklace again.

"_Something this beautiful deserves to be seen on something worthy of its beauty."_

Blair snapped back to reality and realized she still left Chuck upstairs. Shit.

Blair hastened up the staircase leaping two steps at a time. Dorota was at the top of the stairs carrying a large laundry hamper, "Remember Miss Blair, god always watching."

Blair felt the colour leave her face with mortification. Dorota was like a second mother to her, if she knew-how embarrassing!

Blair opened the door to her room to see her laundry hamper still there, full with her clothes. Relieved knowing she hadn't been in her room yet Blair went to her bed and noticed Chuck sitting up a large smirk on his face.

"Now it's time for you to leave," Blair said sternly.

"Already? Waldorf, Waldorf, "Chuck stood up- thankfully wearing boxers- took her in his arms and kissed her. Blair felt her legs weaken and Chuck spun her around. All of a sudden she was on her back on her comfortable Egyptian down comforter.

"But Chuck you need to go," Blair spoke dazed ," what if Dororta saw? Or my mother?" So yes her mother was in Paris but you never know when she'd return.

"Don't worry Waldorf," Chuck said in between kisses. He removed her silk white see through robe and his kisses started to travel south down to her neck and so forth.

Okay so he was allowed to stay for five more minutes, Blair decided.

* * *

A/N: Review please!


	10. Ten

A/N: Wow! Thanks again for all the constant reviews throught this whole story! Seriously you guys continue to amaze me!

Disclaimer: I do not own Gossip Girl or any of its Characters

* * *

Okay, so five minutes turned into over a couple hours but at three o'clock Chuck finally left. Blair knew that through all of her instincts she should not have been doing what they did. Her mind said no, but her body… well it had other ideas.

Blair showered and was about to catch up on her advanced functions math homework, when she got a text from Chuck.

_What are you doing right now?_

_-C_

Being the stalker he was, of course he'd want to know, Blair thought. It's been what, two hours?

Maybe now would be the time to mess with him.

_Just took a shower- why? Are you stalking me for some reason?_

_-B_

Blair smirked and sent the message. A couple seconds later he responded.

_Pity I missed it. And no I was going to ask you if you wanted do our essays together._

-C

Shit! Blair thought after skimming over his text. Blair totally forgot about having to complete that. In her defense she had been a little pre occupied but a few other things. Just a few.

And if Blair wanted to make sure she got into Yale, she had to make sure all her marks were high. Not one bad mark or mistake could happen. It would destroy everything.

_You actually doing school work? Since when?_

_-B_

_I was trying to come up with an excuse to see you again._

_-C_

Blair smirked. Of course the Bass had an ulterior motive.

_Since when did that ever stop you b4?_

_-B_

_Good point. I'll be there in 10._

_-C_

Blair rolled her eyes and got back to doing some of her math work. Just as he promised, ten minutes passed when Dorota called, "Miss Blair, Mr. Chuck for you!"

Blair rose from her desk, checked her reflection quickly before heading downstairs.

"Waldorf, long time no see," Chuck grazed Blair's arm but Blair slapped it away playfully.

"You know I like it rough Waldorf," Chuck smirked.

Of course. Blair rolled her eyes; he was in all of his Chuck Bass glory.

Sure they were in a sense together now but one burning question came to Blair's mind. Where did this leave them?

They weren't a couple but they were now more than friends, yet they weren't friends with benefits. It was complicated.

"Something on your mind Waldorf? You look baffled," Chuck said interrupting her thoughts and again was able to see through her well worn mask.

"Well I was just wondering what this thing between us is," Blair knew he felt the same thing she did last night. You can't exactly fake it.

"Last time I checked we are friends. To me you are considered one of my best friends. I thought that was kind of obvious."

"I know that, it's just well after this week I don't think we are just friends anymore."

"Well we are what you want us to be Waldorf."

Wait was he insinuating that he wanted to be in a relationship with her? Blair knew she was the forbidden fruit but still.

Back up, Blair thought in her head, this is Chuck Bass after all, and Chuck Bass doesn't do relationships. It was silly of her for even assuming that was what he meant.

Okay she definatly misunderstood. Blair did not utter a word for a couple seconds thinking of what they were. Or what they could be. She had two options. One, they could pretend this never happened and remain friends. Defiantly hard to do at this point. Or two, keep this a secret and just be what they are. Whatever they are.

Blair thought about it and made her decision. There really was one solution, "Let's just keep this a secret between you and me Bass. Our little secret," Blair leaned in and kissed Chuck. She knew that they couldn't just deny what was there. Been there done that, and going public about this would never happen. She wasn't ready to even think of going that far with Chuck. That would be the biggest scoop of the year undoubtedly.

During the passionate kiss, Blair felt something flutter in her stomach. Butterflies. Not that she'd tell anyone.

They broke apart when Chuck responded," It'll be difficult keeping this a secret Waldorf, with Gossip Girl everywhere we turn."

Blair smirked," Are you up for the challenge Bass?"

"I'm game," Chuck smirked.

"I knew you would."

"With you Waldorf? Do you really have to ask?" Chuck leaned down and kissed her passionately again.

Blair pulled back, "But on one condition."

Chuck looked puzzled,"What would that be?"

"No other girls. Ever," Blair spoke seriously.

Chuck smirked, "There hasn't been any since Tuesday."

Blair couldn't help a smile form on her face. Chuck continued, "I'm fairly certain those terms are reasonable."

"Good," Blair replied. Her arms rested comfortably around Chuck's neck and she found herself leaning in to kiss him again.

Who knew that she'd be in a… secret relationship with anyone-let along Chuck Bass? Who knew that Chuck Bass could be kind, supportive and caring? This was simply too weird for Blair to comprehend. Chuck Bass was no hero by any means but he was one of her best friends. They knew each other and were able to read each other like an open book. All of this revealed because of this Perfect Match simulation. Crazy.

And who knows, maybe just maybe Chuck Bass was her Perfect Match after all?

Even though Blair would not acknowledge it at that moment in her life, she knew the answer to that.

THE END

* * *

A/N: And that's the end folks! I know some of you might have unanswered questions with Blair's bulimia and such but I feel like that is something on-going with her and wouldn't be resolved just yet at this time. So are you shocked that this is end for this fic? Let me know what you thought in a review!


End file.
